Isosteviol - CAS 27975-19-5
Catalog number: 27975-19-5
Category: Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C20H30O3
Molecular Weight:
318.45
COA:
Inquire
Targets:
Others
Description:
A tetracyclic diterpenoid with a beyerane core has drawn attention because it can exhibit antihypertensive activity, reduce blood glucose, suppress cancer cells.
Purity:
>98%
Synonyms:
(-)-Isosteviol; iso-Steviol
MSDS:
Inquire
InChIKey:
KFVUFODCZDRVSS-XGBBNYNSSA-N
InChI:
InChI=1S/C20H30O3/c1-17-9-5-14-18(2)7-4-8-19(3,16(22)23)13(18)6-10-20(14,12-17)11-15(17)21/h13-14H,4-12H2,1-3H3,(H,22,23)/t13-,14-,17-,18+,19+,20-/m0/s1
Canonical SMILES:
CC12CCC3C4(CCCC(C4CCC3(C1)CC2=O)(C)C(=O)O)C
1. Unfolded and macrocyclic ammonium derivatives of diterpenoids steviol and isosteviol having choline moieties. Synthesis and inhibitory activities toward acetylcholine- and butyrylcholinesterases
Mayya G. Korochkina, Alexandra D. Nikitashina, Ravil N. Khaybullin, Vladimir E. Kataev*. Med. Chem. Commun., 2012, 3, 1449
Ent-beyeran diterpenoid isosteviol 2 (ref. 6a) (ent-16-oxo-beyeran-19-oic acid) is ranked among the most perspective naturally occurring scaffolds for affording novel bioactive compounds. It possesses antihypertension, hypotension, antihyperglycemic, insulinotropic, glucanostatic, anti-proliferation, cardio- and neuroprotective effects, prevents the growth of cancer cells6k,l and exhibits tuberculostatic activity. About 100 isosteviol derivatives of various structures have been covered in the literature, many of them being bioactive. For example, lactone derivatives of isosteviol demonstrate anti-inflammatory activity; functionalization of isosteviol by introducing a double bond at C15, by interconversions in ring D and by coupling of two isosteviol molecules with an amide linker led to novel ent-beyeran-type anticancer agents, functionalization of isosteviol with azine, hydrazide, hydrazone moieties provided a new type of antituberculosis agents. Recently diterpenoid isosteviol 2 was furnished with a choline moiety Me3N+–CH2CH2–O– and the obtained derivatives exhibited high antimicrobial activity. It is known that alkyl-ammonium compounds represent a considerable class of selective reversible inhibitors of cholinesterase. We considered that it would be interesting to investigate whether ammonium derivatives of diterpenoid isosteviol having acetylcholine-like structure in which an acyl group is replaced with bulky isostevioyl moiety show anti-cholinesterase activity. In our opinion, the approach to design novel inhibitors of AchE (BchE) on the basis of naturally occurring terpenoids functionalized by choline moiety or even only ammoniumgroup seems to be original for the following reasons.
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CAS 27975-19-5 Isosteviol

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